CHEM 2020 Chapter 4 Study Guide F19 PDF

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Chapter 4 Study Guide...

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CHEM 2020 Study Guide Chapter 4: Stereochemistry: 3D Structure in Molecules

By the end of Chapter 4 you should be able to: 1. 2. 3. 4. 5. 6. 7. 8. 9.

Determine whether a molecule is chiral or achiral Identify chiral centres in a molecule Determine if a chiral centre is an “R” or “S” conformation using the Cahn-Ingold-Prelog system Be able to use inversions and double inversions to draw enantiomers and alternative views of molecules Distinguish between stereoisomers that are enantiomers and those that are diasteriomers Calculate the maximum number of stereoisomers given the number of chiral centres Recognize meso compounds Name alkenes using the E/Z and cis/trans nomenclature as appropriate Draw Fischer projections and use the D/L nomenclature where appropriate

Recommended End of Chapter Problems: Pg. 179-185, # 4.29, 4.32, 4.33, 4.37, 4.43, 4.55. Questions within the Chapter for Practice (solutions are at the back of the book) 4.1. Determine which of the following molecules are chiral.

4.2. Determine which of the following compounds are chiral. a) prapan-2-ol

b) 1-bromo-1-chloro-ethane

c)1,3-dimethylcyclopent-3-en-1-ol

4.5. Locate all of the chiral centres in the following molecules.

4.6. There are 14 constitutional isomers of C 5H12O. Draw all 14 structures and determine which of them contain at least 1 chiral centre.

4.7. Determine if the chiral centres in the following molecules are "R" or "S".

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CHEM 2020 Study Guide Chapter 4: Stereochemistry: 3D Structure in Molecules 4.8. Draw the R enantiomer of each of the following compounds. a) 1-iodoprop-2-en-1-ol

b) 1-fluoro-1-methoxyethan-1-amine

4.9. Determine if the chiral centre in the following molecules are R or S.

4.10. Draw the S enantiomer of each of the following molecules a) 3-(tert-butyl)-3-isoprpylpent-1en-4-yne

b) 1-formylcyclohex-2-ene-1-carboxylic acid

4.11. Determine the configuration (R or S) at each chiral centre in the following molecules

4.12. Draw the enantiomer of each compound in question 4.11. 4.13. Classify each pair of stereoisomers as either enantiomers or diastereomers

4.14. Classify each pair of structures as either enantiomers, diastereomers, constitutional isomers, or identical compounds.

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CHEM 2020 Study Guide Chapter 4: Stereochemistry: 3D Structure in Molecules 4.17. Classify each of the following compounds a chiral or achiral and as meso or non-meso compounds.

4.18. When asked to draw and name the stereoisomers of pentane-2,4-diol, you might mistakenly list both (2R,4S)-pentane-2,4-diol and (2S,4R)- pentane-2,4-diol. Explain what is wrong with this answer and correct in.

4.28. Convert each of the following amino acids to a Fischer projection and determine whether they are (l) or (D) enantiomers.

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